Skin care gel containing flavonoid compounds and preparation method thereof

Abstract

The invention relates to the technical field of skincare gel, and discloses skincare gel containing flavonoid compounds and a preparation method thereof.The skincare gel containing the flavonoid compounds is obtained by adding chalcone, ethanedione, imidazole modified chitosan, sodium alginate, carrageenan and modified silicone oil into a stirrer and stirring. Quaternary ammonium salt contained in the skin care gel damages cell membranes, cell contents are leaked, cell death is caused, the antibacterial effect is achieved, imidazole groups in the skin care gel can damage integrity and stability of fungal cell membranes, fungal death or growth blocking is caused, and the good antibacterial effect is achieved; wherein the sodium sulfonate, the chitosan and the sodium alginate also have a relatively good antibacterial effect and jointly form an antibacterial system; wherein chalcone, ethanedione and silicone oil groups have a better anti-oxidation effect.

Description

Technical Field

[0001] The invention relates to the technical field of skin care gels, in particular to a skin care gel containing flavonoid compounds and a preparation method thereof. Background Art

[0002] At present, antibacterial gels and antibacterial agents have been developed on the market, but their preparation process is cumbersome and accompanied by the problem of unsatisfactory effect. Therefore, how to avoid this phenomenon is the key to solving the problem. For example, patent CN111888430B discloses a composite antibacterial gel and its preparation method and application. The composite antibacterial gel has an inhibitory effect on Staphylococcus aureus, Escherichia coli, Candida albicans and Candida glabrata, and has a good application prospect, but its antioxidant effect on the skin is not improved. Summary of the invention

[0003] 1. Technical issues to be resolved

[0004] In view of the deficiencies of the prior art, the present invention provides a skin care gel containing flavonoid compounds and a preparation method thereof, which has good skin care antioxidant and antibacterial effects.

[0005] (II) Technical solution

[0006] To achieve the above-mentioned purpose, the present invention provides the following technical solutions: a skin care gel containing flavonoid compounds and a preparation method thereof, a skin care gel containing flavonoid compounds, comprising the following components by weight: 1-3 parts by weight of chalcone, 2-4 parts by weight of ethoxybenzone, 3-5 parts by weight of imidazole-modified chitosan, 1-4 parts by weight of sodium alginate, 2-6 parts by weight of carrageenan, and 4-7 parts by weight of modified silicone oil;

[0007] The preparation method of the modified silicone oil is as follows: adding 5-12 parts by weight of hydrogenated silicone oil and 7-15 parts by weight of olefinated chitosan into N,N-dimethylformamide solvent, stirring and dispersing, adding 1-2 parts by weight of chloroplatinic acid catalyst, reacting at 70-90° C. for 8-15 hours, and then performing rotary distillation and washing to obtain the modified silicone oil.

[0008] Preferably, the preparation method of the imidazole-modified chitosan is:

[0009] (1) adding chitosan to a dimethyl sulfoxide solvent to dissolve it, heating it in a water bath at 60-95° C., adding 2,3-epoxypropyltrimethylammonium chloride at a constant pressure, reacting it for 4-8 hours, washing it with anhydrous ethanol after the reaction, drying it, dialyzing it, and concentrating it to obtain quaternized chitosan;

[0010] (2) adding quaternized chitosan and acrylic acid to N,N-dimethylformamide solvent, stirring evenly, then adding p-toluenesulfonic acid catalyst thereto, reacting at 80-100° C. for 10-13 hours, and then distilling under reduced pressure, filtering and drying to obtain olefinated chitosan;

[0011] (3) adding olefinated chitosan, 2-methyl-1-vinylimidazole, and dimethylaminoethyl methacrylate to N,N-dimethylformamide solvent, stirring and mixing, and continuously adding ammonium persulfate initiator, reacting at 75-100° C. for 7-15 hours, and then rotary distilling and washing to obtain an intermediate;

[0012] (4) adding the intermediate and sodium 3-chloro-2-hydroxypropanesulfonate to a sodium hydroxide aqueous solution with a mass fraction of 3-6%, reacting at 55-75° C. for 6-8 hours, cooling after reaction, adding hydrochloric acid dropwise to adjust the pH to 7, heating and evaporating for recrystallization, and obtaining imidazole-modified chitosan.

[0013] Preferably, the mass ratio of chitosan to 2,3-epoxypropyltrimethylammonium chloride in (1) is 1:1.6-2.2.

[0014] Preferably, the mass ratio of quaternized chitosan, acrylic acid and p-toluenesulfonic acid catalyst in (2) is 1.1-1.3:1:0.02-0.03.

[0015] Preferably, the mass ratio of olefinated chitosan, 2-methyl-1-vinylimidazole, dimethylaminoethyl methacrylate and ammonium persulfate initiator in (3) is 1:1.1-1.3:1.4-1.6:0.03-0.05.

[0016] Preferably, the mass ratio of the intermediate to sodium 3-chloro-2-hydroxypropanesulfonate in (4) is 1.3-1.5:1.

[0017] Preferably, the preparation method of the skin care gel containing flavonoids is: adding chalcone, ethoxybenzone, imidazole-modified chitosan, sodium alginate, carrageenan, and modified silicone oil into a stirrer, stirring for 5-8 minutes, and obtaining the skin care gel containing flavonoids.

[0018] (III) Beneficial technical effects

[0019] The invention prepares the skin care gel containing flavonoid compounds by adding chalcone, ethanolide, imidazole-modified chitosan, sodium alginate, carrageenan and modified silicone oil into a stirrer and stirring the mixture.

[0020] The quaternary ammonium salts contained in the skin care gel destroy the cell membrane, causing the leakage of cell contents and leading to cell death, thereby achieving an antibacterial effect. The imidazole groups therein will destroy the integrity and stability of the fungal cell membrane, leading to fungal death or growth stunting, thereby achieving a good antibacterial effect. The sodium sulfonate, chitosan and sodium alginate therein also have good antibacterial effects and together constitute an antibacterial system; the chalcones, ethoxypropane and silicone oil groups therein have good antioxidant effects. DETAILED DESCRIPTION

[0021] Example 1

[0022] (1) adding chitosan to a dimethyl sulfoxide solvent to dissolve it, heating it in a water bath at 60° C., adding 2,3-epoxypropyltrimethylammonium chloride at a constant pressure, wherein the mass ratio of chitosan to 2,3-epoxypropyltrimethylammonium chloride is 1:1.6, reacting for 4 hours, washing with anhydrous ethanol after the reaction, drying, dialyzing, and concentrating to obtain quaternized chitosan;

[0023] (2) adding quaternized chitosan and acrylic acid to N,N-dimethylformamide solvent, stirring evenly, and then adding p-toluenesulfonic acid catalyst thereto, wherein the mass ratio of quaternized chitosan, acrylic acid, and p-toluenesulfonic acid catalyst is 1.1:1:0.02, reacting at 80° C. for 10 h, and then performing reduced pressure distillation after completion, filtering, and drying to obtain olefinated chitosan;

[0024] (3) Adding olefinated chitosan, 2-methyl-1-vinylimidazole, and dimethylaminoethyl methacrylate to N,N-dimethylformamide solvent, stirring and mixing, and continuously adding ammonium persulfate initiator, wherein the mass ratio of olefinated chitosan, 2-methyl-1-vinylimidazole, dimethylaminoethyl methacrylate, and ammonium persulfate initiator is 1:1.1:1.4:0.03, reacting at 75° C. for 7 h, and then rotary distilling and washing to obtain an intermediate;

[0025] (4) adding the intermediate and sodium 3-chloro-2-hydroxypropane sulfonate to a 3% sodium hydroxide aqueous solution, wherein the mass ratio of the intermediate to sodium 3-chloro-2-hydroxypropane sulfonate is 1.3:1, reacting at 55° C. for 6 hours, cooling after completion, adding hydrochloric acid dropwise to adjust the pH to 7, heating and evaporating for recrystallization, and obtaining imidazole-modified chitosan;

[0026] (5) adding 5 parts by weight of hydrogenated silicone oil and 7 parts by weight of olefinated chitosan to N,N-dimethylformamide solvent, stirring and dispersing, and continuously adding 1 part by weight of chloroplatinic acid catalyst, reacting at 70° C. for 8 h, and then rotary distilling and washing to obtain modified silicone oil;

[0027] (6) Add 1 part by weight of chalcone, 2 parts by weight of ethoxypropane, 3 parts by weight of imidazole-modified chitosan, 1 part by weight of sodium alginate, 2 parts by weight of carrageenan, and 4 parts by weight of modified silicone oil into a blender and stir for 5 minutes to obtain a skin care gel containing flavonoid compounds.

[0028] Example 2

[0029] (1) adding chitosan to a dimethyl sulfoxide solvent to dissolve it, heating it in a water bath at 95° C., adding 2,3-epoxypropyltrimethylammonium chloride at a constant pressure, wherein the mass ratio of chitosan to 2,3-epoxypropyltrimethylammonium chloride is 1:2.2, reacting for 8 hours, washing with anhydrous ethanol after the reaction, drying, dialyzing, and concentrating to obtain quaternized chitosan;

[0030] (2) adding quaternized chitosan and acrylic acid to N,N-dimethylformamide solvent, stirring evenly, and then adding p-toluenesulfonic acid catalyst thereto, wherein the mass ratio of quaternized chitosan, acrylic acid, and p-toluenesulfonic acid catalyst is 1.3:1:0.03, reacting at 100° C. for 13 h, and then distilling under reduced pressure, filtering, and drying to obtain olefinated chitosan;

[0031] (3) Adding olefinated chitosan, 2-methyl-1-vinylimidazole, and dimethylaminoethyl methacrylate to N,N-dimethylformamide solvent, stirring and mixing, and continuously adding ammonium persulfate initiator, wherein the mass ratio of olefinated chitosan, 2-methyl-1-vinylimidazole, dimethylaminoethyl methacrylate, and ammonium persulfate initiator is 1:1.3:1.6:0.05, reacting at 100° C. for 15 h, and then rotary distilling and washing to obtain an intermediate;

[0032] (4) adding the intermediate and sodium 3-chloro-2-hydroxypropane sulfonate to a 6% sodium hydroxide aqueous solution, wherein the mass ratio of the intermediate to sodium 3-chloro-2-hydroxypropane sulfonate is 1.5:1, reacting at 75° C. for 8 h, cooling after completion, adding hydrochloric acid dropwise to adjust the pH to 7, heating and evaporating for recrystallization, and obtaining imidazole-modified chitosan;

[0033] (5) adding 12 parts by weight of hydrogenated silicone oil and 15 parts by weight of olefinated chitosan to N,N-dimethylformamide solvent, stirring and dispersing, and continuously adding 2 parts by weight of chloroplatinic acid catalyst, reacting at 90° C. for 15 h, and then rotary distilling and washing to obtain modified silicone oil;

[0034] (6) 3 parts by weight of chalcone, 4 parts by weight of ethoxypropane, 5 parts by weight of imidazole-modified chitosan, 4 parts by weight of sodium alginate, 6 parts by weight of carrageenan, and 7 parts by weight of modified silicone oil were added into a blender and stirred for 8 minutes to obtain a skin care gel containing flavonoid compounds.

[0035] Example 3

[0036] (1) adding chitosan to a dimethyl sulfoxide solvent to dissolve it, heating it in a water bath at 77° C., adding 2,3-epoxypropyltrimethylammonium chloride at a constant pressure, wherein the mass ratio of chitosan to 2,3-epoxypropyltrimethylammonium chloride is 1:1.9, reacting for 6 hours, washing with anhydrous ethanol after the reaction, drying, dialyzing, and concentrating to obtain quaternized chitosan;

[0037] (2) adding quaternized chitosan and acrylic acid to N,N-dimethylformamide solvent, stirring evenly, and then adding p-toluenesulfonic acid catalyst thereto, wherein the mass ratio of quaternized chitosan, acrylic acid, and p-toluenesulfonic acid catalyst is 1.2:1:0.025, reacting at 90° C. for 11 hours, and then performing reduced pressure distillation after the reaction, filtering, and drying to obtain olefinated chitosan;

[0038] (3) Adding olefinated chitosan, 2-methyl-1-vinylimidazole, and dimethylaminoethyl methacrylate to N,N-dimethylformamide solvent, stirring and mixing, and continuously adding ammonium persulfate initiator, wherein the mass ratio of olefinated chitosan, 2-methyl-1-vinylimidazole, dimethylaminoethyl methacrylate, and ammonium persulfate initiator is 1:1.2:1.5:0.04, reacting at 85° C. for 11 h, and then rotary distilling and washing to obtain an intermediate;

[0039] (4) adding the intermediate and sodium 3-chloro-2-hydroxypropane sulfonate to a 4% sodium hydroxide aqueous solution, wherein the mass ratio of the intermediate to sodium 3-chloro-2-hydroxypropane sulfonate is 1.4:1, reacting at 65° C. for 7 h, cooling after completion, adding hydrochloric acid dropwise to adjust the pH to 7, heating and evaporating for recrystallization, and obtaining imidazole-modified chitosan;

[0040] (5) adding 8 parts by weight of hydrogenated silicone oil and 11 parts by weight of olefinated chitosan to N,N-dimethylformamide solvent, stirring and dispersing, and continuously adding 1.5 parts by weight of chloroplatinic acid catalyst, reacting at 80° C. for 11 h, and then rotary distilling and washing to obtain modified silicone oil;

[0041] (6) Add 2 parts by weight of chalcone, 3 parts by weight of ethoxypropane, 4 parts by weight of imidazole-modified chitosan, 2 parts by weight of sodium alginate, 4 parts by weight of carrageenan, and 5 parts by weight of modified silicone oil into a blender and stir for 6 minutes to obtain a skin care gel containing flavonoid compounds.

[0042] Example 4

[0043] (1) adding chitosan to a dimethyl sulfoxide solvent to dissolve it, heating it in a water bath at 95° C., adding 2,3-epoxypropyltrimethylammonium chloride at a constant pressure, wherein the mass ratio of chitosan to 2,3-epoxypropyltrimethylammonium chloride is 1:2.2, reacting for 8 hours, washing with anhydrous ethanol after the reaction, drying, dialyzing, and concentrating to obtain quaternized chitosan;

[0044] (2) adding quaternized chitosan and acrylic acid to N,N-dimethylformamide solvent, stirring evenly, and then adding p-toluenesulfonic acid catalyst thereto, wherein the mass ratio of quaternized chitosan, acrylic acid, and p-toluenesulfonic acid catalyst is 1.3:1:0.03, reacting at 100° C. for 13 h, and then distilling under reduced pressure, filtering, and drying to obtain olefinated chitosan;

[0045] (3) Adding olefinated chitosan, 2-methyl-1-vinylimidazole, and dimethylaminoethyl methacrylate to N,N-dimethylformamide solvent, stirring and mixing, and continuously adding ammonium persulfate initiator, wherein the mass ratio of olefinated chitosan, 2-methyl-1-vinylimidazole, dimethylaminoethyl methacrylate, and ammonium persulfate initiator is 1:1.2:1.5:0.04, reacting at 85° C. for 11 h, and then rotary distilling and washing to obtain an intermediate;

[0046] (4) adding the intermediate and sodium 3-chloro-2-hydroxypropane sulfonate to a 4% sodium hydroxide aqueous solution, wherein the mass ratio of the intermediate to sodium 3-chloro-2-hydroxypropane sulfonate is 1.4:1, reacting at 65° C. for 7 h, cooling after completion, adding hydrochloric acid dropwise to adjust the pH to 7, heating and evaporating for recrystallization, and obtaining imidazole-modified chitosan;

[0047] (5) adding 5 parts by weight of hydrogenated silicone oil and 7 parts by weight of olefinated chitosan to N,N-dimethylformamide solvent, stirring and dispersing, and continuously adding 1 part by weight of chloroplatinic acid catalyst, reacting at 70° C. for 8 h, and then rotary distilling and washing to obtain modified silicone oil;

[0048] (6) Add 1 part by weight of chalcone, 2 parts by weight of ethoxypropane, 3 parts by weight of imidazole-modified chitosan, 1 part by weight of sodium alginate, 2 parts by weight of carrageenan, and 4 parts by weight of modified silicone oil into a blender and stir for 5 minutes to obtain a skin care gel containing flavonoid compounds.

[0049] Comparative Example 1

[0050] 1 part by weight of chalcone, 2 parts by weight of ethoxyquinone, 3 parts by weight of imidazole-modified chitosan, 1 part by weight of sodium alginate, and 2 parts by weight of carrageenan were added into a blender and stirred for 5 minutes to obtain a skin care gel containing flavonoid compounds.

[0051] Comparative Example 2

[0052] 1 part by weight of chalcone, 2 parts by weight of ethoxypropane, 1 part by weight of sodium alginate, 2 parts by weight of carrageenan, and 4 parts by weight of modified silicone oil were added into a blender and stirred for 5 minutes to obtain a skin care gel containing flavonoid compounds.

[0053] Using Staphylococcus aureus, Escherichia coli or Candida albicans as the test bacteria, 0.5 mL of the bacterial suspension of the test bacteria (concentration of 1×110 CFU / mL) was added to a sterile culture dish containing MH broth medium, and then the skin care gel sample containing flavonoids was attached to the surface of the culture medium, and cultured in a constant temperature incubator at 35°C for 18 h. After culture, the diameter of the inhibition zone was measured.

[0054] Table 1: Antimicrobial testing.

[0055]

[0056] It can be seen from Table 1 that Examples 1-4 of the present invention have better antibacterial function than Comparative Examples 1-2.

[0057] DPPH was dissolved in ethanol to prepare a solution with a concentration of 0.1 mmol / L. The skin care gel containing flavonoids was added to the DPPH solution. After reacting at room temperature for 25 minutes, the change in absorbance was measured at 517 nm to calculate the DPPH free radical scavenging rate.

[0058] Ultrapure water was used to prepare 7 mmol / L ABTS solution and 2.45 mmol / L potassium persulfate solution, mixed in a ratio of 1:1, allowed to stand at room temperature for 14 h, diluted with phosphate buffer solution to an absorbance of 0.7-0.8 at 734 nm to obtain ABTS free radical working solution, and polypeptides with antibacterial and antioxidant functions were added to the ABTS free radical working solution. After reacting at room temperature for 5 min, the absorbance change was measured at 734 nm to calculate the ABTS free radical scavenging rate.

[0059] Table 2: Antioxidant capacity test.

[0060]

[0061] It can be seen from Table 2 that Examples 1-4 of the present invention have better antioxidant function than Comparative Examples 1-2.

[0062] The preferred embodiments of the present invention disclosed above are only used to help illustrate the present invention. The preferred embodiments do not describe all the details in detail, nor do they limit the invention to the specific implementation methods described. Obviously, many modifications and changes can be made according to the content of this specification. This specification selects and specifically describes these embodiments in order to better explain the principles and practical applications of the present invention, so that those skilled in the art can understand and use the present invention well. The present invention is limited only by the claims and their full scope and equivalents.

Claims

1. A skin care gel containing flavonoids, characterized in that: The invention comprises the following components by weight: 1-3 parts by weight of chalcone, 2-4 parts by weight of ethoxybenzone, 3-5 parts by weight of imidazole-modified chitosan, 1-4 parts by weight of sodium alginate, 2-6 parts by weight of carrageenan, and 4-7 parts by weight of modified silicone oil; The preparation method of the modified silicone oil is as follows: adding 5-12 parts by weight of hydrogenated silicone oil and 7-15 parts by weight of olefinated chitosan into N,N-dimethylformamide solvent, stirring and dispersing, adding 1-2 parts by weight of chloroplatinic acid catalyst, reacting at 70-90° C. for 8-15 hours, and then performing rotary distillation and washing to obtain the modified silicone oil.

2. The skin care gel containing flavonoids according to claim 1, characterized in that: The preparation method of the imidazole-modified chitosan is: (1) adding chitosan to a dimethyl sulfoxide solvent to dissolve it, heating it in a water bath at 60-95° C., adding 2,3-epoxypropyltrimethylammonium chloride at a constant pressure, reacting it for 4-8 hours, washing it with anhydrous ethanol after the reaction, drying it, dialyzing it, and concentrating it to obtain quaternized chitosan; (2) adding quaternized chitosan and acrylic acid to N,N-dimethylformamide solvent, stirring evenly, then adding p-toluenesulfonic acid catalyst thereto, reacting at 80-100° C. for 10-13 hours, and then distilling under reduced pressure, filtering and drying to obtain olefinated chitosan; (3) adding olefinated chitosan, 2-methyl-1-vinylimidazole, and dimethylaminoethyl methacrylate to N,N-dimethylformamide solvent, stirring and mixing, and continuously adding ammonium persulfate initiator, reacting at 75-100° C. for 7-15 hours, and then rotary distilling and washing to obtain an intermediate; (4) adding the intermediate and sodium 3-chloro-2-hydroxypropanesulfonate to a sodium hydroxide aqueous solution with a mass fraction of 3-6%, reacting at 55-75° C. for 6-8 hours, cooling after reaction, adding hydrochloric acid dropwise to adjust the pH to 7, heating and evaporating for recrystallization, and obtaining imidazole-modified chitosan.

3. The skin care gel containing flavonoids according to claim 2, characterized in that: The mass ratio of chitosan to 2,3-epoxypropyltrimethylammonium chloride in (1) is 1:1.6-2.

2.

4. The skin care gel containing flavonoids according to claim 2, characterized in that: The mass ratio of quaternized chitosan, acrylic acid and p-toluenesulfonic acid catalyst in (2) is 1.1-1.3:1:0.02-0.

03.

5. The skin care gel containing flavonoids according to claim 2, characterized in that: The mass ratio of olefinated chitosan, 2-methyl-1-vinylimidazole, dimethylaminoethyl methacrylate and ammonium persulfate initiator in (3) is 1:1.1-1.3:1.4-1.6:0.03-0.

05.

6. The skin care gel containing flavonoids according to claim 2, characterized in that: The mass ratio of the intermediate to sodium 3-chloro-2-hydroxypropanesulfonate in (4) is 1.3-1.5:

1.

7. A method for preparing a skin care gel containing flavonoid compounds according to any one of claims 1 to 6, characterized in that: The preparation method of the skin care gel containing flavonoid compounds is as follows: chalcone, ethoxybenzone, imidazole-modified chitosan, sodium alginate, carrageenan and modified silicone oil are added into a stirrer and stirred for 5-8 minutes to obtain the skin care gel containing flavonoid compounds.

Images